Tetrahydrofuran → HCID 90941707, compound

HRID 1800586Notes

Reaction equation

HRID 1800586 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=2)[C:11]([F:24])=[CH:10][C:9]=1[F:25])([CH3:4])([CH3:3])[CH3:2].O1CCCC1>CO.[C].[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=2)[C:11]([F:24])=[CH:10][C:9]=1[F:25])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 91243757HCID 91243757, compound

Product 1

HCID 90941707HCID 90941707, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of tert-butyl{2,4-difluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (10.10 g, 27.5 mmol) and 10% palladium-carbon (5.0 g) in methanol (50 mL)-tetrahydrofuran (50 mL) was vigorously stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was poured into water (200 mL), and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined dried over anhydrous sodium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was crystallized from acetonitrile to give the title compound (8.70 g, 94%) as a white powder.

Workup

  1. filtrationThe insoluble material was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was poured into water (200 mL)
  4. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  5. dry with materialThe ethyl acetate layers were combined dried over anhydrous sodium sulfate
  6. filtrationthe insoluble material was filtered off
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-57e164095df2421e85814623db31cfd7
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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